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Alternative Solvents for Catalysis and Organic Reactions

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Alternative Solvents for Catalysis and Organic Reactions ALTERNATIVE SOLVENTS FOR CATALYSIS AND ORGANIC REACTIONS A Thesis Presented to The Academic Faculty By Vittoria Madonna Blasucci In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in Chemical & Biomolecular Engineering Georgia Institute of Technology December 2009 ALTERNATIVE SOLVENTS FOR CATALYSIS AND ORGANIC REACTIONS Dr. Charles A. Eckert, Advisor School of Chemical & Biomolecular Engineering Georgia Institute of Technology Dr. Charles L. Liotta, Co-Advisor School of Chemistry & Biochemistry Georgia Institute of Technology Dr. William Koros School of Chemical & Biomolecular Engineering Georgia Institute of Technology Dr. Christopher Jones School of Chemical & Biomolecular Engineering Georgia Institute of Technology Dr. Amyn Teja School of Chemical & Biomolecular Engineering Georgia Institute of Technology Date Approved: September 30th 2009 For my Mom and Dad- Without them I would have never made it through ACKNOWLEDGEMENTS First, I would like to acknowledge my advisor, Prof. Charles Eckert. Under his guidance, I was given the freedom to take my research into the areas that interest me the most. Not only is he a valuable information source, but he is also an excellent mentor. In addition, I thank my co-advisor, Prof. Charles Liotta. It has been my pleasure to work with someone who truly loves what they do and refreshing to see somebody who enjoys science so much. Due to these two professors, my time at Georgia Tech has been excellent. I greatly appreciate the time and advice of my committee members: Professors Amyn Teja, Bill Koros, and Chris Jones. Thank you for reading through and editing this document! I would also like to acknowledge Dr. Gelbaum for his assistance with several NMR experiments and a former co-worker from Chevron, Robert Shong, who ran oil analysis experiments. I am especially grateful to the past and present Eckert/Liotta research group members. They have been enjoyable to work with and have become life-long friends. I specifically want to acknowledge two colleagues who greatly contributed to my research: Jason Hallett and Megan Donaldson. I appreciate the laboratory assistance from Georgina Schaefer, an undergraduate researcher. I wouldn’t have been able to make it through my PhD without the help of my friends and family. My mother and father have supported me throughout my academic career. Even though it took longer than they expected, I finally made my dream come true! Thank you to my sister, Dr. Madelena Blasucci, who has always been there. The iv strength of my uncle, Michael Blasucci (1959-2009), taught me to fight through even the worst of situations. Special thanks to Krystle Chavez for her friendship and to Zainul Husain for his friendship and entertainment during long lab days. Lastly, but most importantly, I would like to thank God for always keeping an eye over me and blessing me each day. v TABLE OF CONTENTS ACKNOWLEDGEMENTS ............................................................................................... iv LIST OF TABLES ............................................................................................................. xi LIST OF FIGURES .......................................................................................................... xii LIST OF SCHEMES........................................................................................................ xvi NOMENCLATURE ....................................................................................................... xvii SUMMARY ...................................................................................................................... xx CHAPTER 1. INTRODUCTION .......................................................................................1 1.1. References ........................................................................................................... 4 CHAPTER 2. ONE-COMPONENT, SWITCHABLE IONIC LIQUIDS DERIVED FROM SILYLATED AMINES ...........................................................................................5 2.1. Introduction ......................................................................................................... 5 2.2. Materials ............................................................................................................. 7 2.3. Experimental Methods ........................................................................................ 8 2.3.1 Ionic Liquid Formation ............................................................................... 8 2.3.2 Hydrosilylation Reactions ........................................................................... 9 2.3.3 Viscosity Experiments ................................................................................ 9 2.3.4 Nile Red Polarity Tests ............................................................................. 10 2.3.5 Differential Scanning Calorimetry (DSC)/Thermal Gravimetric Analysis (TGA) …………………………………………………………………………... 10 2.3.6 Crude Oil Purification Proof of Principle Recycles .................................. 10 2.3.7 Carbon Capture Capacity .......................................................................... 11 2.3.8 Stability Tests............................................................................................ 12 vi 2.3.9 Scale-up Simulations ................................................................................ 12 2.4. Results ............................................................................................................... 13 2.4.1 Siloxylated Amines ................................................................................... 13 2.4.2 Application to Hydrocarbon Extraction from Crude Oil .......................... 27 2.4.3 Silylated Amine Synthesis and Characterization ...................................... 32 2.4.4 Amine Stability ......................................................................................... 43 2.4.5 Application to Carbon Capture from Post-Combustion Flue Gas Streams ………………………………………………………………………….. 46 2.4.6 Intramolecular Interaction: Siloxylated Amine Precursors....................... 49 2.5. Conclusions ....................................................................................................... 54 2.6. References ......................................................................................................... 55 CHAPTER 3. HOMOGENEOUS CATALYSIS COUPLED WITH BENIGN SEPARATION IN POLYETHYLENE GLYCOL-ORGANIC-TUNABLE SOLVENT SYSTEMS …………………………………………………………………………... 58 3.1. Introduction ....................................................................................................... 58 3.2. Materials ........................................................................................................... 66 3.3. Experimental Methods ...................................................................................... 67 3.3.1 Reaction of 2-chloro-p-xylene and potassium hydroxide to produce 2,5-di- methylphenol in POTS .............................................................................................. 67 3.3.2 Reaction of 1-bromo-3,5-di-tert-butylbenzene with potassium hydroxide to produce 3,5-di-tert-butylphenol in POTS ............................................................. 68 3.3.3 Reaction of 2-chloro-p-xylene with basic salts to produce 1,1’-oxybis[2,5- dimethyl]benzene ...................................................................................................... 69 3.3.4 Reaction of 2-chloro-p-xylene with phenol and basic salts to produce 2,5- dimethyl-1-phenoxybenzene ..................................................................................... 70 3.3.5 Reaction of 1-bromo-3,5-di-methylbenzene and o-cresol with potassium hydroxide to produce o-tolyl-3,5-xylyl ether in POTS ............................................. 70 vii 3.3.6 Separation of 3,5-di-tert-butylphenol using POTS ................................... 71 3.3.7 Separation of o-tolyl-3,5-xylyl ether using POTS .................................... 72 3.3.8 Separation of PdL12 using POTS .............................................................. 72 3.3.9 Sweeping Carbon Dioxide Extraction of 2,4-di-methylphenol and o-tolyl- 3,5-xylyl ether from PEG 400 ................................................................................... 74 3.4. Results ............................................................................................................... 74 3.4.1 C-O coupling to produce phenols ............................................................. 74 3.4.2 C-O coupling to produce aromatic ethers ................................................. 82 3.4.3 Sweeping CO2 ........................................................................................... 87 3.4.4 Partitioning ................................................................................................ 88 3.5. Conclusions ....................................................................................................... 94 3.6. References ......................................................................................................... 95 CHAPTER 4. FUNCTIONALIZATION OF ETHYLENIC POLYMERS WITH SILANES …………………………………………………………………………. 98 4.1. Introduction ....................................................................................................... 98 4.2. Experimental Methods .................................................................................... 102 4.2.1 Materials ................................................................................................
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